IP Library › Granted Patent US 11,732,281
Granted Patent B2
US 11,732,281 · App. 17/464,887 · Granted Aug 22, 2023

Methods for making L-glufosinate

Inventors: Brian Michael Green (Lutherville, MD); Michelle Lorraine Gradley (Canterbury, GB)
Assignee: BASF SE
C12P13/02A01N25/30A01N57/20C12N1/20C12N9/10C12P9/00C12P13/04C12P41/00C12Y104/03003C12Y206/01019
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Quick Facts
Patent No.
US 11,732,281
App. No.
17/464,887
Granted
Aug 22, 2023
Kind
B2
Abstract

Methods for the production of L-glufosinate (also known as phosphinothricin or (S)-2-amino-4-(hydroxy(methyl)phosphonoyl)butanoic acid) are provided. The methods comprise a two-step process. The first step involves the oxidative deamination of D-glufosinate to PPO (2-oxo-4-(hydroxy(methyl)phosphinoyl)butyric acid). The second step involves the specific amination of PPO to L-glufosinate, using an amine group from one or more amine donors. By combining these two reactions, the proportion of L-glufosinate in a mixture of L-glufosinate and D-glufosinate can be substantially increased.

Claims (17)

1. A herbicidal formulation, wherein said formulation comprises L-glufosinate at an enantiomeric excess of greater than 90% over D-glufosinate, and more than 0.01% but less than 10% PPO (2-oxo-4-(hydroxy(methyl)phosphinoyl)butyric acid), said formulation further comprising at least one adjuvant.

2. The formulation of claim 1 , wherein said adjuvant is selected from a surfactant, a solvent, a polysaccharide humectant, and a diluent.

3. The formulation of claim 2 , wherein said surfactant is sodium alkyl ether sulfate.

4. The formulation of claim 2 , wherein said solvent is selected from at least one of 1-methoxy-2-propanol, dipropylene glycol, and ethylene glycol.

5. The formulation of claim 2 , wherein said polysaccharide humectant is selected from at least one of alkyl polysaccharides, pentoses, high fructose corn syrup, sorbitol, and molasses.

6. The formulation of claim 2 , wherein said diluent is an aqueous component.

7. The formulation of claim 2 , wherein said diluent is water.

8. The formulation of claim 1 , wherein said L-glufosinate composition comprises L-glufosinate ammonium in an amount from 10-30% by weight of the formulation; and wherein said adjuvant comprises one or more additional components selected from the group consisting of sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation; 1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation; dipropylene glycol in an amount from 4-18% by weight of the formulation; and alkyl polysaccharide in an amount from 4-20% by weight of the formulation; and water as the balance of the formulation.

9. The formulation of claim 1 , wherein the L-glufosinate composition comprises L-glufosinate ammonium in an amount of 12.25% by weight of the formulation; and wherein said adjuvant comprises sodium alkyl ether sulfate in an amount of 31.6% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; dipropylene glycol in an amount of 8.6% by weight of the formulation; alkyl polysaccharide in an amount of 9.8% by weight of the formulation; and water in an amount of 36.75% by weight of the formulation.

10. The formulation of claim 1 , wherein the L-glufosinate composition comprises L-glufosinate ammonium in an amount of 24.5% by weight of the formulation; and wherein said adjuvant comprises sodium alkyl ether sulfate in an amount of 31.6% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; dipropylene glycol in an amount of 8.6% by weight of the formulation; alkyl polysaccharide in an amount of 9.8% by weight of the formulation; and water in an amount of 24.5% by weight of the formulation.

11. The formulation of claim 1 , wherein the L-glufosinate composition comprises L-glufosinate ammonium in an amount of 12.25% by weight of the formulation; sodium alkyl ether sulfate in an amount of 15.8% by weight of the formulation; 1-methoxy-2-propanol in an amount of 0.5% by weight of the formulation; dipropylene glycol in an amount of 4.3% by weight of the formulation; alkyl polysaccharide in an amount of 4.9% by weight of the formulation; and water in an amount of 62.25% by weight of the formulation.

12. The formulation of claim 1 , wherein the L-glufosinate composition comprises L-glufosinate ammonium in an amount from 10-30% by weight of the formulation; and wherein said adjuvant is selected from one or more additional components selected from the group consisting of sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation; 1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation; and alkyl polysaccharide in an amount from 3-10% by weight of the formulation; and water as the balance of the formulation.

13. The formulation of claim 1 , wherein the L-glufosinate composition comprises L-glufosinate ammonium in an amount of 12.25% by weight of the formulation; and wherein said adjuvant comprises sodium alkyl ether sulfate in an amount of 22.1% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; alkyl polysaccharide in an amount of 6.2% by weight of the formulation; and water in an amount of 58.45% by weight of the formulation.

14. The formulation of claim 1 , wherein the L-glufosinate composition comprises L-glufosinate ammonium in an amount of 24.5% by weight of the formulation; and wherein said adjuvant comprises sodium alkyl ether sulfate in an amount of 22.1% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; alkyl polysaccharide in an amount of 6.2% by weight of the formulation; and water in an amount of 46.2% by weight of the formulation.

15. The formulation of claim 1 , wherein the L-glufosinate composition comprises L-glufosinate ammonium in an amount of 12.25% by weight of the formulation; and wherein said adjuvant comprises sodium alkyl ether sulfate in an amount of 11.05% by weight of the formulation; 1-methoxy-2-propanol in an amount of 0.5% by weight of the formulation; alkyl polysaccharide in an amount of 3.1% by weight of the formulation; and water in an amount of 73.1% by weight of the formulation.

16. A method for selectively controlling weeds in an area comprising applying an effective amount of the formulation of claim 1 to the area.

17. The method of claim 16 , wherein said area comprises a crop of planted seeds or crops that are resistant to glufosinate.

Continuity (8)
Continuation 16997133 · Aug 19, 2020
Continuation 16287290 · Feb 27, 2019
Continuation 15787448 · Oct 18, 2017
Division 15445254 · Feb 28, 2017
Provisional Application 62413240 · Oct 26, 2016
Provisional Application 62336989 · May 16, 2016
Provisional Application 62302421 · Mar 2, 2016
Related Publication 20210395790A1 · Dec 23, 2021